


Princess of Hell and her Warrior of Heaven

by DemonDeepFried



Category: Supernatural
Genre: Crowley has a daughter, F/M, First Time, Getting Together, Goddesses, Major Original Character(s), Non-Canon Couple Ficathon, OC, Original Character(s), POV Original Character, Slow Build, Slow Build Castiel/Dean Winchester, Trickster Gabriel, Trickster Loki, Tricksters, Undercover as a Couple, princess of hell
Language: English
Status: In-Progress
Published: 2015-02-22
Updated: 2015-03-19
Packaged: 2018-03-14 12:09:26
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Rape/Non-Con
Chapters: 7
Words: 16,900
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3410087
Author URL: https://archiveofourown.org/users/DemonDeepFried/pseuds/DemonDeepFried
Summary: <blockquote class="userstuff">
              <p>Jay is a petite 20 year old woman with long pink hair and an odd obsession for gummy bears and flower crowns.<br/>But she is also a hunter.<br/>And she is also Crowley's daughter, making her the Princess of Hell.</p><p>Bobby, Dean, Sam, Castiel and Gabriel are her real family now; they're the ones who mean the most to her and she is willing to fight for that...especially for Gabriel...<br/>When a hunt requires Jay and Gabriel to pretend to be a couple for their stay at a romantic couples' retreat, it is almost too much for her but can her feelings be suppressed for their stay or will they bubble to the surface when they meet the one enemy that could bring all of their secrets to the surface?</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> So, this was a fanfic request from one of our followers on our tumblr account (spnimagineandfanfic) Crowleysprincess159 invented Jay's character (and she did a fantastic job!) and I wrote the rest of the fanfic at her request.  
> If any of you do have a request for any supernatural fanfic whatsoever, please message me either on here or on our account which can be found by following this link: http://spnimagineandfanfic.tumblr.com/ (if you cannot click the link you can paste it into your URL)  
> Hope you enjoy :)

** _2015_ **

"Sorry I'm late, darlings," she smiled, wickedly.

The woman stood at the entrance to the abandoned warehouse was a woman like no other, even if you didn't know about what blood coursed through her veins. Vibrant pink hair cascaded in subtle curls over her shoulders and down her back, contrasting against her large, dark brown eyes that twinkled in the moon light spilling through a gap in the ceiling. She had a petite but curvy figure of 5'5 and wore a pair of slim fitting black jeans beneath knee-high biker boots threaded with dark laces. Under a black leather jacket, she wore a deep fuchsia vest top with lighter lace patterns just above the hem; from her earlobes hung short black earrings that matched the black glass beads on her bracelet. Her skin tone was a mix between tanned and pale, and if you looked closely enough you could see faint freckles spotting her quaint nose. The woman possessed a cherub shaped face that resembled a doll in proportion to her features.

But she was no doll.

She was a fierce hunter of Team Free Will.

She was Crowley's daughter; the Princess of Hell.

She was a demon/human/witch hybrid.

She was Jay.

And she was pissed.

With a smirk that carried no humour, she flicked her wrist and the two rings of burning holy fire that surrounded Gabriel and Castiel, dissipated into nothing.

The three demons, that were guarding the angels, leapt up and growled at the intruder.

"What're you looking at, demon dick?" she snapped at the foremost demon that was brandishing a shining knife- the knife she knew belonged to Sam Winchester.

The demon cocked his head and frowned warily. "You're...you're the Princess..."

"Give the man a cookie," she congratulated sarcastically, clapping her hands together for a moment before lunging forwards and throwing the miserable creature across the barren warehouse and into an iron wall.

Sharing a look that said  _well, now we're fucked_ , the two demons turned back to Jay as though they were confused as to what their next move should be. But before they could decide, Castiel and Gabriel were behind them with an angel blade piercing their meat suits' flesh. With a scream and a blazing orange light that stuttered from their eyes and mouths, they died.

Retracting their blades, the angels turned back to Jay. "Jay!" Gabriel greeted. "Took your time!"

With a genuine smile, the Princess focused her gaze on the archangel. His mousey brown hair was slightly ruffled but his hazel eyes remained bright and- though she convinced herself it was just a figment of her dire hope- seemed to sparkle a little when they locked on hers. "Sorry, sweetheart, you know traffic is a nightmare."

The archangel chuckled and threw a glance at Castiel, checking his well-being, before announcing, "So, looks like we're gonna have to save Bad Boys' asses again."

Castiel frowned momentarily, missing the reference to the action film, but cleared his expression with a deep exhale as he turned towards the back of the warehouse to point at a far door. "They're through there."

It took less than ten minutes to  _rescue_  Sam and Dean, and get out of the crumbling building, stabbing the first demon as they went.

 

After packing up all their belongings from the motel into the glossy '67 Chevy Impala, the five hunters decided unanimously that they deserved a well-earned drink.

Heading towards the bar, a block over, Jay noted that the roadhouse they entered was called  _Mackenzie's_.

She patted the brothers on the back as she stepped through the door and told them, "Beers are on me, honeys."

Jay sidled up to the counter, leaving the rest of Team Free Will- Sam, Dean, Cas and Gabe- to find a booth, and quirked her full red lips into a smile.

"Well, hello there, darling," she greeted the bartender- a man of about 20 with a stature of muscle, handsomeness and a hint of arrogance.

"Well hello, and what can I do for you, Miss?" he shot back, a flirtatious smirk plastered on his face, which was chiseled like a model and bristling with purposely trimmed stubble.

"A round of five beers," she ordered sweetly, "if you don't mind."

The bartender finished drying the glass he held and returned her smile with a similar one of his own, flashing perfect white teeth that didn't look right on a bartender that probably earned five bucks a week. "Coming right up," he promised. "I'll bring them to your table."

She thanked him and turned around to try and find the booth where the boys were sitting in. It took her a minute before she spotted Gabriel waving his hand at her through the small crowd surrounding the small static TV in the corner. Jostling her way through the shuffling bodies, she inwardly cursed human men and resisted the urge to snap a neck or two when a cheer rocked the whole party backwards and some beer got spilt on her jacket.

"Urgh," Jay huffed as she slumped down into the seat that Sam offered. "Humans."

"Well don't look at me," Gabriel gasped in mock offense. 

The small group chuckled quietly at that, before the discussion of the case Dean had found in Georgia arose.

Unfolding a newspaper, Dean laid the article out and began to explain it. "So, three couples have gone missing at this couples' retreat thing. One of the couples showed up a week after they went missing. It looks like they were stabbed to death, but the thing is that when the cops went to identify the weapon, it was some kind of blade they've never seen before. Left burn marks and all sorts of messed up looking crap."

"OK..." Gabriel interrupted. "So some psycho is getting it on with a knife and lighter, that doesn't sound like us."

Sam rolled his eyes. "Dude, we've gone further for less."

With a sigh and a barely concealed grumble, Jay input, "Well, people are dying right, and isn't it kinda our job to stop any evil things doing that?"

"Yeah, I know." Gabriel scratched the back of his neck. "Was only wondering, is all. So, we setting off tonight then?"

"God no, I'm shattered," Jay interjected, cracking her neck and trying to stifle a yawn. "We can set off tomorrow morning."

"Right," Dean agreed. "So, for tonight let's have a beer or two, hustle some pool and pick up some girls."

The party laughed hushedly again... but it didn't escape Jay's keen eye, the muscle that jumped in Castiel's jaw and his lips became a thin line. She frowned and tilted her head a little, discreetly, at the tightness that settled in the angel's ocean blue irises.

But she put the thought out of her mind when the bartender came over to their table, placing a metal tray laiden with five beer bottles on the dark wood.

"There you go, ma'am," he smiled, whisking Jay's bottle into the air. "Allow me," he grinned crookedly, wielding a bottle opener that he aimed towards Jay's drink.

"Oh, that's no problem-" she tried to tell him but he was already struggling with the cap. "Yeah, OK then..." she grimaced and winced a bit as he visibly grunted under the effort of...just...pulling...a cap off- wait a minute.

She sent a sharp look in Gabriel's direction and saw him trying to hide a smirk.

"Gabe!" she hissed and he shot a  _what?!_  look. She narrowed her eyes a little, gesturing her head slightly at the bartender who was actually breaking a sweat trying to open the bottle.

The archangel sighed dramatically and subtly clicked his fingers under the table, the minute he did so almost caused the bartender to fall over as the cap sprung effortlessly off the bottle. This consequently caused the rest of the table to try and suppress their laughter.

Clearing his throat, the bartender handed Jay the drink and shuffled self-consciously away, leaving the table to their own devices after that.

" _Gabe_ ," Jay moaned, the corners of her lips quirking upwards uncontrollably and ruining the message she had been trying to deliver.

"What?" he grinned back, shrugging his shoulders. "The guy was arrogant. It's called  _just desserts_ , I  _am_  the trickster after all."

She couldn't help but smile at that. "Trickster or no trickster," Jay spoke to Gabriel. "You still can't mess with people just for the fun of it."

"Oh, can't I?" he retorted and Jay felt her hair pulling itself upwards and dancing around her head.

This resulted in another course of laughter around the table as everyone reached for their drinks and knocked the caps off on the edge of the table or twisted them off by hand.

Jay quirked her eyebrows, challenging. "Oh it's on, sweetheart," she warned, her voice teasing. Flicking her wrist, Gabriel coughed suddenly and then a  _cluck_  bubbled out of between his lips.

His eyes went wide and he opened his mouth again, only for another  _cluck_ to come out.

Dean burst into laughter and managed to gasp out, "Oh my God,  _never_  turn that off!"

Gabriel scowled and let out another, more frustrated, chicken  _bacaw_ before Jay reluctantly snapped her fingers and gave him his voice back.

She was crying from her laughter by the time Gabriel managed to bite out, rather bitterly, "Yeah, well, archangel/trickster still trumps demon." He sipped his drink and avoided Jay's smug eye contact.

"Everything trumps demon," she shot back, sipping her own drink. "But kickass demon/witch/human... _that_  trumps all."

Sam and Dean grinned before returning to their beers, and the table split into several different conversations: Sam with Cas, Jay with Gabriel, and Dean with a woman from the next booth.

The night carried on like that until the hunters eventually returned to the motel- Dean and Sam sleeping in one room, Cas and Gabriel watching a documentary in the next (criticizing every fact that they knew was wrong), and Jay left alone to toss and turn in another.

With a heavy sigh, she grunted and rolled over again. 

She detested being alone, especially in bed- not in a sexual way, more in a lonely way.

* * *

 

Jay was the daughter of the King of Hell, Crowley. Consequently, the blood that ran her veins was a beautifully powerful mixture of demon, human and witch. 

5 years ago, when she was only fifteen years old, Crowley had come to her adoptive home in Lincoln, Nebraska to take her to Hell where she would 'become the rightful Princess'. 

But Jay had refused. 

Therefore it had taken little more than an exasperated sigh and an elaborate click of his fingers before both Jay's adoptive parents were lying dead on the floor.

However that had done nothing but fuel her hatred of her demon father and she had resolved to the hunting life, discovering her awe-inspiring powers along the way.

Two years ago, she met Sam and Dean at Bobby's house in Sioux Falls where she had followed a demon called Meg who was on a killing spree.

Though bursting in through the door to confront the demon had done little to soften the brothers or Bobby's nerves, she had saved Dean and Bobby's lives from the demon that was controlling Sam. She had offered a quick explanation before expelling the demon from Sam's body with just a command, 'Get out of him, you black eyed bitch.'

Then just as she was trying to leave, Bobby had stopped her and asked her, 'So, who are you, kid?'

Jay's reply had been no more than, 'Nobody. I'm not someone to keep around.'

But the brothers and their almost surrogate father had argued enough that she had reluctantly obliged and taken them up on the offer of free beer.

After passing every test that Bobby laid on her, they unanimously decided that she was safe to keep around and had taken her under their wing, effectively naming her one of their small patch-worked family.

And she had never looked back.

* * *

 

"Rise and shine, Candy Floss," Gabriel cooed early next morning, flinging the curtains that covered Jay's windows wide open to allow the blinding sunlight to burst through.

Jay hissed menacingly and with an animalistic edge that came from being part witch and part demon, and also from general hatred of early mornings.

With a primal growl, she snarled, "You better bring me a coffee, pronto."

Gabriel replied only with a fond chuckle before leaving the room in a ripple of light that came as a perk of being a trickster.

"And there better be gummy bears waiting for me!" she yelled into the now-empty room, but she could faintly hear the archangel's amused compliance.

It took Jay only thirty minutes to shower, brush her teeth and get dressed into the clothes she wore yesterday- favouring putting her leather jacket over her arm instead though because it was a hot morning.

She grabbed her wash bag and decided to put her makeup on in the car- and she would  _not_  be sitting bitch again.

As Jay left the room, she cursed under her breath when she remembered her adoptive mother's necklace which was still laid carefully on her bedside table. With a sharp click of her fingers, it flew across the room and into her outstretched palm.

 

"Morning sweethearts," Jay greeted her small family as she clambered gracelessly into the passenger seat. "Aw, you remembered, Gabe.  _Il mio angelo custode,_ " she smiled gratefully and almost lovingly- though totally  _not!-_ at the archangel behind her when she spotted the packet of gummy bears and travel cup of coffee on the dashboard. Jay was fluent in Italian, thanks to her father (though she wouldn't willingly admit her tutor) and had got into the habit of calling Gabriel  _her guardian angel_  in said tongue- mainly because she loved nicknames but also because it sent a slight flush across his face that was positively endearing...

"Yeah, yeah, save the romance and get that off my baby's dash," Dean snapped as he pulled the driver's door closed behind him, making sweeping motions with his hands at the steaming travel cup. "What were you born in a barn? Get that coffee off her dash before it leaves a mark!"

With a fond chuckle, Jay obliged and took the cup and packet onto her lap. "Alright, honey, your car's OK," she promised, shooting the older Winchester a teasing but reassuring look.

Through an obviously fake cough, Gabriel added unhelpfully, "For now."

Dean shot the archangel a withering glare that made him sit back, even more amused, with his hands held up in surrender. "Nothing by it, Dean-o, nothing by it. Now come on, let's get-a moving!"

"We gotta wait for Cas yet," Dean told them, turning back around and slotting a tape into the deck.

Led Zeppelin's  _Ramble On_  was just starting as Sam folded his massive frame into the Impala and announced, "Cas is gonna meet us there, he...has stuff to do?"

"What exactly does an angel cut off from Heaven,  _have to do_?" Jay wondered, but she didn't miss the small flicker of hurt in Dean's expression.

"Hey!" Gabriel protested. "I got plenty to do, thank you very much."

Jay shot a snort over her shoulder, to which she earned a swatting from the archangel.

"Right, well, come on Baby," Dean murmured to the wheel as he hefted up the handbrake and started the engine.

 

Throughout the journey, Jay and Gabriel traded witty remarks back and forth, pausing only for Jay to eat a gummy bear or throw one in Gabe's direction.

Dean was adamant about getting to Georgia before nightfall but Jay managed to convince him to pull over at a service station to get some food and more beer. Reluctantly, he had rolled his eyes and pulled into the car park.

Jay was the first one to dash up the short stack of staircase and into the large building, heading straight for WHSmith's where she grabbed a large armful of gummy bears and thrust them all in the arms of the slightly bewildered cashier.

He totalled the amount, sneaking dubious glances towards the vast amount, and packed them all into a plastic bag.

"And this!" Jay heard Gabe announce behind her, before a hand came around her waist to dump a porn mag and a massive bag of lollipops on the counter. 

" _Gabe_ -!" she moaned but was interrupted again by Dean coming up behind her to throw  _another_ porn mag and a cased box of pie into the cashier's hands.

"Add this, too!" he called as he joined Gabe outside.

" _Dean-_!" she groaned, but was this time cut off by Sam appearing by her shoulder to drop a newspaper and a box of salad on the counter.

"Thanks, Jay," he thanked as he bounded off to the other boys' sides.

"OK...now that's..." Jay struggled as she twisted around to face the boys. "I don't know which of those is unhealthier than the other."

Dean grinned and clapped his hand on his brother's shoulder. "Sammy gets off in his own way."

Sam shrugged him off but there was a smile tugging absently at his lips. "Get off, Dean. I'm checking the papers for any cases and  _yes_ , I like to eat healthy because have you seen how many chemicals are in pie?"

"No, I haven't," Dean replied. "I just read  _pie_."

Jay smiled at her boys before turning back to the cashier and accepting the two bags and vaguely bemused look he handed to her.

* * *

** _2007_ **

The third hunt Jay joined the brothers on was in Ohio, investigating a strange suicide off a high floor at a university.

It was one of the university professors; an old bloke who took the swan dive for no reason anyone was aware of. Via further digging into student rumours, the trio had managed to uncover adulterous secrets that left all three of them debating whether or not his mysterious death was really something that desired investigating. 

And then they were told about the legend surrounding room 669- which immediately made Jay giggle- the girl who died in there or something. Jay passed it off as bull but they dug it up anyway and she sat back while Sam and Dean searched around for some bones to burn.

Even by the second day, Jay was finding the brothers' actions towards each other  _hilarious_.

She was lounging quite happily on the motel sofa, nursing a bottle of beer, watching the two bicker about Sam's missing laptop and Dean's slashed tires.

Jay didn't think she'd ever laughed so hard when they actually started wrestling on the bed.

There was another incident that involved a frat boy swearing up and down that he was abducted by aliens and...probed...a lot. 

They were sitting down at a table in the bar talking to the frat boy and Jay was having real trouble hiding her stuttering laughter as he continued to tell them about his experience with the  _aliens._

Frankly, Jay thought it was fucking comical that the aliens made him slow dance! And she told him as much, much to Sam's disapproval.

Before Bobby arrived- at her pleading- there was one other case in the same town when an animal tester (Jay couldn't remember the actual terminology) was eaten by an alligator.

It wasn't until Bobby showed up that any of it started to make sense.

"You got a trickster on your hands," he'd told them.

"That's what I thought," Dean told them straight away.

"What?!" Sam had exclaimed. "You did not!"

Jay just giggled and shared an amused look with Bobby.

By that point, the three men still didn't know what it who Jay really was but she had no inclination to tell them just yet.

Bobby explained what a trickster was to them and so they went out to hunt the thing with their stakes. Sam and Dean seemed positive that the trickster was the janitor they spoke to at the university, the one that Jay hadn't met yet.

When Sam, Bobby and Jay arrived at the university later that night, after Dean's ingenious plan to trick the trickster, their stakes were poised as they entered the hall.

Jay could clearly see the trickster sitting in one of the seats of the bleachers. At her entrance with Bobby and Sam, the trickster turned around and-

The Princess of Hell felt her breath hitch and her heart stutter.

The trickster's expression changed from smugness to something akin to wonder. A frown pulled at his eyebrows for a second but then the trickster displayed the only genuine thing he had since the first time he met Sam and Dean, he smiled. It was a small smile that only quirked his lips a little but it shone in his eyes and echoed through the room until the blood roared in her ears and lights shone too brightly in her eyes. 

Then, everything dissipated into nothing, and that was all there was.

And in that moment, she felt her soul- quite uncontrollably- bare itself before his...

But then of course, she went and stabbed him in the chest, which didn't exactly spark chemistry.

* * *

** _2015_ **

They finally arrived at the couples' retreat several hours later, long into the night and Jay was struggling to keep her eyes open.

"What exactly are our identities, here?" she mumbled through a fog of fatigue.

"Uhh, yeah, about that," Dean started, running his hand through his hair.

"Dean..." She narrowed her eyes, a warning note in her tone.

"Well, it  _is_ a  _couples_ ' retreat thing," he tried.

"Ah," a female voice came from the top of a set of cream painted stone steps surrounded by tropical plants. "Mr Winchester! And this must be Mr and Mrs- umm, Trickster?"

Dean coughed around a laugh. "Yep, yeah, this is Mr and Mrs Trickster," he gestured to Gabriel and Jay. "And this is my brother, Sam, he's come about the job vacancy."

"Oh yes," the woman smiled, she was wearing a blouse with a black pencil skirt and looked to be about 40 with dark hair. "My name's Janet, your partner is inside, Mr Winchester. I hope you enjoy your stay."

"Umm, my-my partner?" Dean looked actually confused now.

"Mr Castiel?" She raised her eyebrows.

Dean's eyes went wide and Gabriel, Jay and Sam had to press their lips together hard to stifle laughter.

"C-Castiel?" Dean stammered. "He told you that...he...and I...?"

"Yes," Janet smiled. "He's just inside, he didn't get here ten minutes ago."

Gabriel wiggled his eyebrows at Sam and Jay. "Who ever said Destiel wasn't a thing."

As Gabe followed Janet and Dean up the stairs, Jay turned to Sam and mumbled, "We should never have introduced him to fanfiction."

"Yeah well, don't get him started on which of Chuck's books is his favourite," Sam groaned, making Jay chuckle. "An hour long discussion, not even including the books that Chuck never published."

"There are more?!" Jay asked excitedly, the Supernatural series had kept Jay very entertained since she'd met the boys.

Sam shot her a dark look. "So Gabe tells us..."

Jay grinned wickedly, "Well, I think I'll be talking to him about that later."

 

"So, Mr and Mrs Trickster?" Janet smiled at Jay and Gabriel from behind her desk.

"Umm, we're not married, it's just Mr...Trickster and Miss Singer," Jay corrected.

Behind her, Dean turned to Sam with a frown and mouthed, ' _Singer_?' To which Sam replied with a shrug.

"But you can just call us Jay and The Trickster," Gabe told her, wrapping his arm around Jay's shoulders.

Jay rolled her eyes. "Gabriel, his name is Gabriel."

"OK, my mistake, welcome to Riverview Couples' Retreat," she smiled at them again, reaching under the desk to retrieve three sets of keys. "Mr Winchester, you're in room 218- sorry, staff don't stay in the commercial rooms." She handed Sam the key and he thanked her briefly.

"Mr Winchester, err, Dean?" she inclined her head towards him.

"Eh? Yeah, yeah it's Dean," he told her, flashing a flirtatious smile.

She returned it and continued, "Dean. This is your and Castiel's key, and you two will be in the Cherub Room. You can find it on the first floor, its the last one on the corridor."

Dean thanked her and turned to hand the key to Castiel, starting slightly when his proximity was less than a hand-span. "Personal space, Cas, personal freakin' space."

The three left Jay and Gabe as they went to search out their own rooms- though not before Gabriel had cracked a joke about Dean making the most of that king sized bed. 

"Jay, Gabriel, you will be staying in the Tropical Suite," Janet beamed at them.

"Ooh," Jay grinned. "Sounds exotic, I like it."

Gabriel looked across at her and chuckled fondly, his smile bleeding warmth.

"It's on the first floor, head that way and its the second door on your left," Janet directed them, angling her hand to her left and bending over the ornate desk to angle her hand the way she directed them.

"Alright, thanks," Jay said to Janet, grabbing Gabe's elbow tightly as she strode away in the direction she was indicated. "What the  _hell_ is wrong with Dean?!"

Gabriel just laughed. "Can't blame Dean-o, who else was he gonna couple you up with? The Sasquatch?"

Jay upturned her lip, cocked her head and raised her eyebrows in a look that considered it with a  _well..._

With a roll of the eyes, Gabe replied, "You really want Gigantor, over  _this?"_ He gestured his hands up and down his body.

She couldn't hide the grin that curled her lips upwards and made her heart swell just a little bit.

 

They found their room without much trouble and made their way inside. True to its name, the room was...well it was tropical.

As soon as Jay flicked on the lights, her eyebrows rose.

"Wow," Jay exclaimed as she stepped into the room. "This. Is.  _Tropical._ "

"Well it is what it says on the label," Gabriel pointed out.

Jay's eyes settled on the king sized bed and she chewed her lip. Gabriel must have noticed because he quickly reassured her, "Oh, I'll take the floor, I don't sleep much anyway."

"Gabe," she frowned. She knew that because he was completely shut off from Heaven and relenting some of his Trickster powers that he did in fact need some sleep.

"What?" he grinned, his trickster persona taking control. "You worried for me? Aw, the Princess has developed a soft spot."

Jay just rolled her eyes and started unpacking her suitcase on the bed.

She was about half way through when she heard Gabriel abandon his own unpacking and step over to her."Woah," Gabe whistled, coming up behind her. "How many beanies does one woman need?"

Jay spun around with a scowl. "You. Can. Never. Have. Enough. Beanies!"

To drive her point home she grabbed two and pulled them over her head. "Example A," she said defiantly, and finished the rest of her packing wearing two beanies.

 


	2. Chapter 2

**Summary for the Chapter:**

> Jay had had to actually drive away the sudden cloud of warmth that drifted over her thoughts with the appearance of a fog and her heart had jumped into her throat of its own accord.  
> But before she could stab him again, he made them a quick deal, promising them that the days would move on and Dean would not die every day.  
> And the day did move on.  
> And Dean didn't die every day.  
> He died once.
> 
> And he didn't come back.

**Notes for the Chapter:**

> So, just a warning, this fic isn't really designated into chapters, it's just parts within the chapters because I'm writing this as a request on tumblr and just keep updating it on here when there's a chance. Just ignore the chapter headings and enjoy :)

** _ 2008 _ **

The next time the trio encountered the Trickster, Sam was losing it a little bit.

They had gone to a town to investigate the suspicious disappearance of a man at a mystery spot. While both Jay and Dean were skeptical, Sam was quite certain that the cause could be the mystery spot itself.

Then Dean got shot.

Being a demon/human/witch hybrid, Jay knew something was up because the powers that were affecting the boys didn't work on her as well as it should have done. Sure, she still experienced Dean's death every day, but her powers weren't as sure as they were normally.

As no one knew about her true species, she left Sam and Dean on their own- or more accurately, she left Sam alone to cope with Dean's reoccurring death every day- to seek out what was happening.

She had still felt it every time Dean died and the days didn't move on from Tuesday for her either but she didn't wake up every time he died like Sam did. Thus making it a hell of a lot easier to keep moving and actually getting somewhere.

After several hundred Tuesdays, Jay reached an answer.

It wouldnt have taken much longwe, though, before she would have had to return to her family- that was the moment she really realised who her true family were, and they were Sam and Dean. 

On her return though she bumped into a man who was being noticeably followed by Sam and Dean.

'Sam! Dean!' she hissed at them.

'Jay?' Sam frowned, then his expression turned to pure relief and he embraced her tightly. 'Where have you been?' he asked her through tears.

'What are you talking about? She was with us this morning?' Dean said.

Ignoring him, Jay explained, 'I'm sorry, I went to find out what this thing is. Sam, it's the Trickster.'

Sam's brow furrowed before his face cleared and he pointed a steady finger towards the man who was walking away from them. 'It's him,' he said firmly and surely.

Jay checked behind her and scrutinised the man. 'You're sure?'

'Yes.' was the answer and that was enough for her.

They cornered him and confronted the Trickster who smirked and admitted, rippling into his true form.

'You got me!' he'd taunted.

Jay had had to actually drive away the sudden cloud of warmth that drifted over her thoughts with the appearance of a fog and her heart had jumped into her throat of its own accord.

But before she could stab him again, he made them a quick deal, promising them that the days would move on and Dean would not die every day.

And the day did move on.

And Dean didn't die every day.

He died once.

And didn't come 

* * *

** _2015_ **

 

"Pig."

"Porky."

"Bugs bunny."

"Carrots."

"Hmm, orange."

"Yellow."

"Red."

"Err...paint."

"Smelly."

Gabriel rolled over where he was lying on the floor at the foot of Jay's bed and laughed. "Your feet!"

"Hey!" Jay snapped, sitting upright in bed and letting the covers slip to her lap. "My feet do  _not_  smell."

Raising his hands in defence, Gabriel returned with, "I'm just saying what comes into my head first, it's kinda the rules of the Word Association Game."

Rolling her eyes, Jay submitted reluctantly and lay back down in bed. The lights were off and their room was submerged in darkness.

The Tropical Room was easily thirty feet by twenty five; the walls were a creamy white and the ceiling had exposed rafters that were a cherry wood. A green glass chandelier hung from the ceiling and matched the bedspread on the king-sized four poster bed.

All around the room were potted plants stood on tables and the floor, and hanging from the walls and rafters were odd plants and vines that resembled those from a rainforest. Flowers covered the majority of the walls and petals were scattered across the floor and the bed.

The bed was pushed against the centre of one wall and in the centre of the room was a plush green rug with colourful patterns. The floor was made of a rough straw like hemming that desired some serious fabric softener. A massive TV was embedded in the wall opposite the bed and Gabriel had assured Jay that there was enough porn to keep a small army entertained.

On the right wall, almost directly opposite the main door- which was beach wood and ringed with vines and flowers- was the identical door that led to the en suite bathroom.

In the bathroom, the floor was hard wood and it was nearly half the size of the main room. A bath big enough for two was centred in the middle of the room; it was a cuboid shape with green glass decorating the four sides and various flowers and vines curling up the edges.

In one corner was an ornate sink with an incredible assortment of lotions, oils and soapy things. In another there was a walk in shower big enough for four with brown tiles and matching green glass to the bath. The toilet was nestled in another corner and had a wood seat and jungle-like leaves plastered over the china body.

On the far side of the bathroom were a set of double doors that led out onto a balcony. The balcony had a wood floor and over looked the Botanical Gardens, ringed with black metal balustrades that were woven with ivy and jungle leaves. Scattered all across the wood floor were more petals and taking up the entirety of one quarter of the balcony deck was a hot tub that was embedded into the deck. Jay hadn't actually been able to contain her excitement upon discovering the hot tub.

"Pfft," Jay dismissed. "My feet still don't smell," she grumbled under her breath.

Gabriel still heard and laughed before relenting,"Yeah, yeah OK."

With a huffed sigh, Jay announced, "Right well I am shattered, so I'm off to sleep."

"Alright, Cupcake, night night," Gabe mumbled, already half-asleep.

Jay smiled into her pillow, she liked it when anyone called her  _cupcake_ , but she loved it when Gabriel called her it.

 

The Princess roused early that next morning due to a sharp rapping on the main door.

"Argh!" she growled, throwing one of the many pillows that sat on her bed at the door in a futile attempt to shut whoever it was the hell up. "Go away!"

"Jay!" She could hear Dean's muffled voice coming through the door. "Come on, Jay-Jay, we got work to do."

"I hate you all," she snarled through her fingers.

"Yeah, yeah," he dismissed, wandering off.

Tossing over and throwing the comforter over herself for dignity, Jay grumbled and rubbed her still-closed eyes with the heel of her hand.

Gabriel whistled. "I underestimated your hair, it can get wilder."

With bleary eyes, she peered into the mirror on her bedside table and had to agree with Gabriel: she did have quite extraordinary bed hair.

"Shh," she silenced him with a finger. "No words until noon."

Gabriel chuckled but cooperated all the same, only after telling Jay that she'd have to wait another five hours before she could hear his magnificent voice again.

Busying herself in the bathroom, Jay showered quickly, brushed her teeth and only bothered putting some quick eyeliner on before she stumbled into the main room to get dressed.

"Out!" she ordered Gabe, pointing firmly at the door to the bathroom.

"What?! Why?" he protested even as she started shoving him into the bathroom.

"I need to get dressed and I'm not comfortable being naked in front trickster/archangels," she told him as she slammed the bathroom door behind him.

"But we're supposed to be a couple..." he whined teasingly. 

"Yeah, yeah,  _Trickster_ ," she rolled her eyes and turned to pull a pair of black leggings and a loose billowy dark lavender summer dress with thin straps out of the chest of drawers she packed her clothes into.

She pulled on her knickers first, then her leggings, twisting the fabric until it was comfortable. Then she clipped the clasp of her bra around her back before tugging on the soft silky material of the summer dress over her head. The fabric bunched up around her breasts and rippled downwards; it was one of her favourite dresses. She knew she didn't have the most desirable figure, she criticised herself often enough to remember, but on her good days- like today- she let go a bit and reminded herself ' _yeah, I am pretty damn sexy._ '

As she settled herself on the small plush stool in front of the mirror, she yelled through to Gabriel, "You can come out now, sweetie!"

Gabriel opened the door to saunter into the room before jumping into the air and flipping onto the four poster bed.

"Hey!" Jay snapped, pausing from where she was dragging a brush through her bright pink hair. "Feet. Off!"

Chuckling to himself, he obliged and shuffled until his feet hung off the edge. "Happy?" He raised his eyebrows.

Jay grunted and returned to her hair, giving up with her tangled mane after five minutes and just tying it in a loose high ponytail. Make-up could go stick itself because she was just  _too_  tired to be putting up with it.

Turning round to Gabriel, he grinned and said, "Looking beautiful, breakfast now?"

And just that one comment made her heart skip and her fall in love with the archangel just a little bit more.

_Damn it._

* * *

  ** _2008_**

Consoling Sam after Dean's final death had been a monstrous task but Jay had managed it- to an extent.

As soon as she had calmed him down enough, he had become obsessed with the task of finding the trickster and driving a stake through his heart. Again.

Jay was desperate to get Sam to calm it and she was using her powers almost daily to serve that. And it was becoming quickly tiring. The hunter would just not give up and, while it tired her to the extent that she would sleep extended periods just to recharge, in all honesty she had to respect that.

"Sam," she begged one night. "Sam, I know what this is to you," she managed through the fatigue that was claiming her as she still fervently tried to sooth the swarm of emotions and driven hatred that was clouding Sam's mind, "but it's killing you and Dean will seriously beat your ass if you die because of him."

"Dammit, Jay!" he suddenly shouted, throwing the gun cleaning kit that was laid out on the table, to the floor in one sweep. 

Jay visibly jumped, shocked and slightly scared- which was ridiculous because he couldn't seriously hurt her even when she was this weak.

Sam saw her fear though and his regret and apology were plastered on his face. "I am so sorry, Jay," he whispered, not even able to look in her direction. "I need to go, I can't keep hurting you. You and Bobby are the only family I have left."

"Sam!" she called as he stepped out of the door. 

He turned briefly to hear her say, "He was my brother, too."

"I know," he nodded, before continuing outside and into the car, driving away to nowhere in particular.

Jay watched the impala speed away into the hazy horizon and sighed. Even as he left her alone in the small dingy motel room, Jay had still seen him as her brother. They both were. 

And family  _always_  came first.

And it didn't always end in blood.


	3. Chapter 3

**Summary for the Chapter:**

> From his jacket pocket, he produced a wooden stake, the point of it soaked in dried blood. Jay was speechless. She didn't know what was right and what was wrong right then. But when Sammy drove that stake into their surrogate father's back, she still gasped.
> 
> "Bobby!"
> 
> Jay knelt down beside him but when she went to touch him, he rippled and disappeared into thin air- trickster work. The stake that had been embedded in him, rattled on the floor where it was left and then zipped upwards and over Sam's shoulder, straight into the hand of...the trickster.

**Notes for the Chapter:**

> Hope you're all enjoying the story, tension's building a wee bit in this chapter! Have fun!

** _2015_ **

"We're going to a  _massage_?" Jay asked again, incredulously.

"We are here by my credit card-" Dean started, waving said card.

"Er, Mr..." Jay swiped the card from him and studied it, " _J U Tuskilinee's_  credit card, more like."

Dean snatched it back. "Yeah, whatever," he muttered, shoving it back into his pocket. "We're still making the most of this weekend."

Jay rolled her eyes and smiled fondly. "Alright, so absolutely nothing to do with the fact that you love scented oils then..."

"What?!" Sam and Gabe spluttered, jumping into the conversation from where they were discussing Heaven with Cas, alerted by the words  _love_ and  _scented oils_ being in the same sentence when describing Dean.

"Oh, thanks a lot, Jay," Dean growled at her.

"You like scented oils?" Sam raised his eyebrows, an incredibly amused smile tugging at his lips.

Dean pushed past both his brother and the archangel, his palms held against them. "It smells nice and it feels good, sue me."

Gabriel and Sam shared a bemused look before following him down to the spa.

But before they went in, Sam stopped and said, "Crap, I was supposed to be down at the gym with a class."

"They have a gym here?" Jay frowned, astonished. "But it's supposed to be a relaxing place?"

Sam shot her an exasperated face that only a sibling could give to another- which made Jay's taunting smile just that bit more genuine- and replied, "Ha ha very funny, but exercise is healthy and-"

"Blah blah blah," Dean cut him off. "Just make sure you at least talk to a girl, don't just stand there all weird."

"What?" Sam protested. "I'm not weird."

Dean, Jay, Gabriel and Cas all cocked their heads to one side.

"Yeah, Sasquatch," Gabriel chimed in, "you kinda are."

Sam huffed his annoyance and stormed off in the other direction.

Stepping inside, the room was completely tiled in cream colours with odd patterns. Dotting around were potted plants with spiky leaves that reminded Jay of when she visited the Rainforest in the Amazon once.

Even the room was oddly shaped, curving around to create a small alcove that only spaced for an inbuilt stone bench.

Before the four was a desk that looked as though it had grown out of the floor and was similarly tiled. Behind it was a woman of about 20, with fair hair strapped back into a bun and a delicate posture accompanied by gleaming smile that must hurt. 

"Can I help you?" she asked nicely, inclining her head towards them.

"Err, yeah, we- err,we're here for the-the massage?" Dean struggled, awkwardly.

It made Jay smile but she tried to hide it from him, his ego had suffered enough damage for today.

"Mr Winchester?" the woman checked, looking at her clipboard.

"Yeah," he affirmed, slipping her a crooked smile.

"OK." She blushed slightly. "And this must be... Miss Singer and Mr Trickster?"

Jay chuckled and hung her head a  bit as she admitted, "I still can't get over:  _Mr Trickster_!"

At the funny look she received from the woman behind the desk, she added quickly, "Honey, sweetheart, babe."

Dean rolled his eyes and Gabe just grinned, totally at ease with the situation. Castiel hadn't moved from Dean's side but even he cracked a small smile.

The woman seemed to skip over the comment and just gestured for them to follow her as she stepped through an arch in the wall.

They followed her and were hit by a wall of heat.

"Geez." Gabriel wheezed against the steam, covering his mouth- something the rest of them copied, apart from Castiel who maintained immune to the humid air.

"Yes, it...takes some getting used to," the woman assured them.

"Huh," Jay huffed behind a hand. "Some getting used to."

Dean nodded in agreement but they carried on down the tiled hall until they reached another room which was concealed by a wood door.

As the woman opened the door, they were hit by another wall, but this one was significantly less humid and rang with the stench of oils.

"Oh," Jay mumbled as the smells of vanilla, jasmine, sandalwood, green tea and all sorts of exotic flavours rippled up to her. "Wow."

There were four other people in the room- one man and three women who all wore matching black tee-shirts and black trousers and skirts- and they all stopped talking to turn to Team Free Will (minus one moose.)

The woman who had led them to the room exchanged a few short words with the man and women before leaving again.

Inside the room, the walls were made of timber and the room itself was easily the size of Gabe and Jay's bedroom. All the objects in the room looked as though they weren't electrical and there were more potted plants dotted around. There were four long tables embedded with plush cushioning and each had a small hole in the centre of the top end- massage tables, Jay recognised them as.

The man- whom was almost Dean's height but had dark hair and dark eyes- smiled and came over to them. "Hey," he greeted them. "My name's Fergus and we'll be your masseuses."

"Awesome," Jay replied, rubbing her hands together. "So...how do we do this exactly?"

"Oh, well, if you just want to strip down to a bathing costume and Hannah will give you a robe to put on," Fergus told them. "Changing rooms are right through there," he informed them, pointing to another door at the end of the room.

"Thanks," Jay smiled at him, taking the robe she was offered. "But, I , uh, I don't have a bathing costume..." She chewed her lip as she admitted it.

"That's no problem, honey," one of the female masseuse reassured her. "We've got some here, they're new so don't worry and you can just hand it right back afterwards."

"Oh thank you ever so much," she thanked the woman who handed the black bikini to her. "You're a saviour."

They got changed quickly and left their clothes in the changing rooms, before returning to the main room. Castiel still didn't understand exactly what was going on despite Dean trying to explain it to him several times. In the end he just told him to lie down with his face in the hole and not to zap anyone when they started touching his back.

As Jay lied down, she groaned at the warm, soft cushioning at her front. The room temperature was comfortable and she basked in it.

She heard Fergus breath a laugh behind her before squirting something into his hands and then rubbing them together to warm it up. The minute his large, silky hands touched her skin, she moaned loudly and embarrassingly.

"Jesus, Jay," Gabriel laughed from his bed next to her. "You sound like a freakin' porn star!"

"Mmshutupmmm," she grumbled, unwilling to sacrifice her relaxation for proper words.

All she got was a chuckle in reply- though there was something forced about it that she frowned at.

 

As they were massaged, Dean and Cas kept querying their masseuses until Dean couldn't actually talk any more because his muscles went so floppy, leaving Cas to it.

So far they had found out that the person who had found the bodies of the first couple to go missing had quit two days afterwards. The woman who told them had shaken her head when Dean had asked her why- she didn't know.

Fergus had added at some point that since about a month ago, there had been random sightings of cats. He swore up and down that they were lynx but Jay had pointed out exactly how likely it was for a lynx to be strolling the streets of Georgia.

Aside from that, they didn't get anything else out of the staff- the massage staff had had very little association with the whole ordeal.

 

* * *

**_2008_**  

Jay followed Sam even after he left her because she couldn't leave him and she couldn't let him go through this alone. He was her brother- blood or not- and until Hell froze over, she wouldn't be abandoning him.

It was a year or so from Dean's death that Sam found the trickster.

He phoned Jay as soon as he found him and she picked up Bobby from his house before meeting him where the whole thing had begun- the mystery spot.

Bobby had explained that the mystery spot was the last place they knew for certain that the trickster used his magic, therefore the best place to fit the bill for the summoning ritual required a gallon of fresh blood, meaning they'd have to bleed a person dry...

"Then let's go get some," Sam said with no hesitation, turning around to leave.

"You break my heart, kid," Bobby whispered.

Sam turned back. "What?"

"Sam," Jay pleaded, her voice sad. "We can't let you murder an innocent man."

"Then why'd you bring me here?" he scowled, his voice annoyed and frustrated.

"Why?" Bobby exclaimed. "Because it was the only way you'd see me! Because I'm trying to knock some sense into you! Because I thought you'd back down from killing a man!"

Jay had a pained look when she said, "I thought you'd understand just what you're doing."

"Well, you thought wrong," the young hunter snapped  "Leave the stuff, I'll do it myself."

"I told you, I'm not gonna let you kill a man." Bobby shook his head.

"It's none of your damn business what I do!" Sam shouted.

"Sam!" Jay yelled back. 

Some vague sort of realisation dawned on his long-haunted face. "Jay..." he mumbled absently. "Look, I'm sorry but I have to do this."

"You want your brother back so bad?" Bobby raised his eyebrows and turned around to retrieve a knife. "Fine."

Sam eyed the knife. "What are you talking about?"

"Better me than a civilian," he said with a half shrug.

"What?!" Jay gasped. "Bobby-!"

"You're crazy, Bobby," Sam exclaimed. "I'm not killing you."

The exchange continued  until Bobby was on his knees facing the sigil that had been painted on the floor and Sam had a knife in his hand.

"Sam," Jay tried again. "Sam, you can't do this."

"You want Dean back too, don't you?" he snapped.

"Of course I do," she replied without hesitation. "But you're about to kill  _Bobby._ "

Sam shot her a knowing look, then gestured towards the old man kneeling before them both. "No, I'm not."

From his jacket pocket, he produced a wooden stake, the point of it soaked in dried blood. Jay was speechless. She didn't know what was right and what was wrong right then. But when Sammy drove that stake into their surrogate father's back, she still gasped.

"...Bobby?" Sam frowned when the body didn't disappear like it should have done.

"Bobby?" Jay repeated. "Bobby!"

Jay knelt down beside him but when she went to touch him, he rippled and disappeared into thin air- trickster work. The stake that had been embedded in him, rattled on the floor where it was left and then zipped upwards and over Sam's shoulder, straight into the hand of...the trickster.

"You're right," he laughed, the sound making Jay stand up quickly and turn around sharply. "I was just screwing with you. Pretty good, though, Sam. Smart. Let me tell you, whoever said Dean was the dysfunctional one has never seen you with a sharp object in your hands. Holy Full Metal Jacket."

"You..." Jay growled- despite what infatuation sang in her heart, Dean, Sam and Bobby were her family, and the trickster was hurting them.

"Me!" he sang, pointing at himself.

"Bring him back," Sam ordered, suddenly.

"Who, Dean? Didn't my girl send you flowers? Dean's dead. He ain't coming back. His soul's downstairs doing the hell fire rumba as we speak," the trickster told him, his voice quite happily emotion-free.

"Just take us back to that Tuesday-er, Wednesday-when it all started. Please. We won't come after you, I swear," Sam begged.

"Sam..." Jay warned. "Think about what you're saying."

"I swear," Sam reiterated, firmly.

"You swear?" The trickster cocked his head ad cracked a smirk that rang with triumph.

"Yes."

"No!" Jay interjected.

"Ooh!" The Trickster cooed. "I sense a domestic!"

Sam ignored them both and repeated himself again. "Yes."

"I dont know..." The Trickster chewed his lip as though turning the idea over in his head. "Even if I could-"

"You can!" growled Sam.

"True. But that don't mean I should," Loki pointed out. "Sam, there's a lesson here that I've been trying to drill into that freakish Cro-Magnon skull of yours."

"Lesson?" Jay frowned incredulously.

"What lesson?" Sam queried, suspiciously.

With a sigh, Loki the Trickster- whom totally  _didn't_ make Jay's heart skip a little every time she came across him- explained exasperatedly, "This obsession to save Dean? The way you two keep sacrificing yourselves for each other? Nothing good comes out of it. Just blood and pain. Dean's your weakness. And the bad guys know it, too. It's gonna be the death of you, Sam and you too, Jay. Sometimes you just gotta let people go."

"He's our brother!" Jay snapped. 

"Yup." The Trickster quirked his eyebrows. "And like it or not, this is what life's gonna be like without him."

"Please," Sam begged, disregarding Loki's words. "Just- please."

"I swear, it's like talking to a brick wall!" The Trickster huffed. "Okay, look. This all stopped being fun months ago. You're Travis Bickle in a skirt, pal. I'm over it."

"Meaning what?" Jay narrowed her eyes.

Loki wiggled his eyebrows. "Meaning that's for me to know and you to find out."

 _Snap_.

At the echoing sound of the Trickster snapping his fingers, Jay and Sam had woken up in bed.

And it was Wednesday.

* * *

** _2015_ **

Team Free Will met up with Sam in the dinner hall after the massage- Gabriel had insisted on getting a meal since they were there and Jay and Dean were starving.

As they sat down, Dean let out a small  _whoop_ of joy when he spotted that the meal prices were included in the room charge- and also because he spotted  _Apple Pie with ice-cream_  on the desserts menu.

Jay reached for her own menu as she settled down in one of the six wooden chairs surrounding the round table covered in a pristine white cloth. Scanning through it, she noted the delicious sounding ravioli and decided immediately that she would have it.

When the waiter came round to their table, Jay ordered, "Umm, can I have the mushroom ravioli with a shed load of cheese and a beer."

"Make that two, my good sir, but steady it on the cheese," Gabriel added.

"Yeah, I think that's five beers and... have you got anything resembling a burger?" Dean asked, expectantly.

The waiter faltered slightly before trying, "Err, I think we may be able to make one...?"

"Awesome, thanks, " Dean thanked casually.

"Dean!" Jay reprimanded. Then, turning to the waiter- who was clearly young and clueless- she told him softly, "It's OK, don't worry about his burger, just bring anything with red meat in it."

The waiter nodded thankfully and turned to Sam who asked for a Caesar salad, then to Castiel who declined altogether. 

At Cas' negatory answer, the waiter twisted subtly towards Jay again, expecting her to offer another counter-answer.

She sighed and said, "Bring him a selection plate and he can pick from that."

She received another nod of gratitude before the waiter scuttled away again to the kitchen.

"Jay, I am a celestial being... I do not require food," Castiel told her when the waiter had left.

"Yeah, I know, sweetheart," she dismissed. "But you don't have to need food to enjoy it."

"B-" Cas started.

"Ah!" she silenced him, holding her finger out to him in a gesture to quieten the angel. "You know you loved those gummy bears I gave you, so keep your celestial pie hole shut on the matter and enjoy the goddamned food."

 

Their meal arrived not long after and the lot of them wolfed it down, including  Castiel. During the meal, they discussed what they had found out. Sam explained that the gym staff only had gossip to give up- but he said that they had seen an unusual amount of cats around, too.

Afterwards, Sam left them to go to his room while Gabe and Jay went with Dean and Cas to theirs.

At their door, Gabriel suddenly smirked at their room, for no apparent reason, and said, "So, Dean-o, you have been making the most of that bed."

Dean's head snapped around at the comment and he glared, in the midst of bewilderment plastered on his face, at Gabriel. "What?" he asked, his voice low, strained and very dangerous curiously.

"Nothing" Gabriel singsonged before wiggling his eyebrows once more and slinking off in the direction of the Tropical Room.

Jay shrugged at Dean and Cas before following Gabriel down the wide, expensively decorated corridor.

 

The Princess fell asleep to the soothing sound of Gabriel quietly humming every classic rock song he knew, at her request because she loved classic rock and it helped her sleep, from where he lay on the floor.


	4. Chapter 4

**Summary for the Chapter:**

> Jay hesitated a moment, her face as emotionless and blank as it could be, and turned back to Gabriel. He was already looking at her. "Family isn't all apple pies and monopoly," she whispered, her voice hushed but dangerous and the archangel listened. "Don't you dare complain about your family. You're fucking blessed." And with that, she turned around and marched straight out of the door, leaving the archangel simmering in his own stew behind her.

**Notes for the Chapter:**

> Some itsy bitsy angst in this one and also a teeny weeny bit of nsfw (but trust me, you'll love it!)  
> For those of you waiting for the 'explicit' rating to come into play, never fear, it will be here soon enough but if you desperately want to read some before then then you can send a request for anything at all to the blog: spnimagineandfanfic on Tumblr!

** _2015_ **

When Jay woke, it was at the harsh patter of water falling. It must be raining outside, she thought.

With a grumble, she rolled over inelegantly and reached blindly for her phone on the bedside table. Finding it, she rolled back over with it clasped safely in her hand, and clicked it on. Hissing at thesudden brightness of her screen, she waited for her eyes to adjust before checking the time.

It was 10:00 am. She sniffed and yawned, stretching stiffly as she clambered out of bed. Dragging a brush through her magenta hair, she wiped her bleary eyes with a face wipe and slumped towards the bathroom door.

Without hesitation, she flung it wide and swore loudly as she took in the sight before her.

"Jesus, Jay!" Gabriel shouted in surprise from where he was showering in the corner...on full-view. "Get out!" He dropped the flannel he'd been holding, in favour of covering his area.

"Oh...my God," Jay bit out before spinning around and being smacked in the ass by Gabriel's magic swiping the door shut with a slam. "Sorry!" she called through the closed door.

All she got was a string of grumbled curses in return, which she agreed she probably deserved. She gulped and slumped to a sitting position against the door.

Even when she pressed her forehead against her knees, the image of Gabriel's glistening naked body in the shower was still etched into her mind. The way the water droplets had defined his muscular frame; the heat that had tinted his skin slightly pink; the delicious scent of his natural musk combined with the exotic flavour of his shampoo; the lustful glint in his eyes- that's colours frequently reminded her of marigolds in a muddy field; the way his hair was tousled a bit from where his hand had been running through it, tugging it; the sinful way he had been digging his teeth into the soft pink of his bottom lip.

And the way his hand had been stroking himself fervidly...

"Dio mio," she groaned into her pyjama clothed knees.

She had definitely crossed that line now and she knew she wouldn't be able to come back from it.

The line that separated pure platonism...

...from unrequited, uncontrollable love.

"Sto così avvitato."

 

"Jay."

Jay turned from where she was nestled in a bundle of blankets facing the TV screen, where The Hairy Bikers was playing.

"Gabe..." she started. "I am so sorry-!"

He chuckled quietly. A quick look saw that he was wearing only a pair of grey sweat pants and his still shining chest was bare. "I'm sorry, I probably should've locked the door." He ran his hand through his wet hair, making it stand up and make Jay want to grab it between her fingers and do sinful things while she tugged on it...

"No shit!" Jay exclaimed, but she was grinning too.

The archangel copied it and advised, "Well, the next time you want to see some hot piece of ass, check out the porn first- we got a butt load of it."

Jay let her head fall into the pillow of blankets on her lap and groaned loudly. "I did not do that purposefully!"

Gabe's laughter rang out in the room. "I know, cupcake, I know."

He finished getting dressed and Jay finished her cooking program before they went downstairs to breakfast, meanwhile discussing whether baking cakes yourself made them taste better. The tension between them vanished, but replaced with a desirous longing that Jay could no longer deny.

But the princess had no fantasy that it could be returned.

 

"Pancakes!" Jay squealed as soon as she walked into the dining hall.

Cas and Dean were already sitting at a table nearest the windows on the far wall. They were in the midst of a heated discussion but broke apart and waved as they spotted Jay and Gabriel.

"Someone took their time this morning," Dean smirked. "Been making the most of that four poster bed or that hot tub?"

Jay rolled her eyes and retorted, "Bet you have."

The Winchester tensed, visibly, which made her frown. 

"Dude, I'm only joking," she assured him. It did little to comfort him but he nodded and the topic dropped with all the grace of a truck carrying two tonnes of bricks.

The first thing to find itself on Jay's plate was a large batch of pancakes which were immediately topped with maple syrup that appeared instantaneously when she swished her index finger in a small circle above the plate. She chewed her lip. "It's still missing something..." she mumbled but she couldn't put her finger on what.

With a chuckle, Gabriel snapped his fingers and a handful of colourful gummy bears bounced from thin air onto her pancakes.

She grinned at him in gratitude. "Il mio angelo custode," she praised him as she took a bite of pancake.

Because her eyes were completely focused on the delicious pancakes in front of her, Jay missed the small loving smile that quirked Gabriel's lips. It was only there for a brief moment before he remembered himself and wiped his face clean of the window that was shining a desperate spotlight on his infatuated soul.

 

* * *

**_2009_**  

The last time Sam, Dean and Jay met the Trickster as they knew him, they were investigating a case in Wellington, Ohio where a man had been supposedly attacked by a bear.

They only figured out they were dealing with a Trickster when the vic's wife swore that it was the Incredible Hulk she had seen tearing her husband's head off.

"Well, it turns out that Bill Randolph had quite the temper. He's got two counts of spousal battery, bar brawls, and court-ordered anger management sessions. You might say you wouldn't like him when he's angry," Dean told them when they were back in the motel.

Sam summarised, "So a hothead getting killed by TV's greatest hothead."

The older Winchester snorted.

"Kinda sounds like just desserts, doesn't it?" Jay added, from her place lying on one of the boys' beds.

"It's all starting to make sense," Sam siad.

"How is it starting to make sense?" Dean frowned.

In answer, Sammy pulled a handful of candy wrappers from his pocket and held them out for the other two to see. "Candy wrappers," he told them, dropping the wrappers onto the bed in front of Jay. "Lots of them."

"Just desserts, sweet tooth, screwing with people before you kill 'em-we're dealing with the Trickster, aren't we?" Dean grumbled.

"Crap," Jay had groaned.

They'd waited next to the police radio, waiting impatiently for any kind of sign that might tell them where the Trickster could be, when they heard the scanner tell dispatch of a  _'_ possible 187' down at the Old Paper Mill on route 6. 

The boys and Jay had barely hesitated before tearing ass to the warehouse, but when they had got there, it was barren.

"There was a murder here, and there's no police cars," Dean mumbled, suspicion creeping into his voice. "There's nobody. How's that look to you?"

Jay shook her head at the dubious situation, it was making her spine tingle and the hairs on her arms were prickling.

"Crappy," Sam answered, accepting the flash light and wooden stake that Dean handed to him.

However, when they entered the warehouse, it was nothing any of them imagined.

"What the-?" Jay mumbled as the three looked around at their surroundings, still trying to process the fact that they were in...a hospital?

Looking down, Jay had seen that she was wearing a long white lab coat, similar to the ones Sam and Dean were wearing.

Two women passed the trio, nodding to the men as they passed. "Doctor." "Doctor."

"Doctor?" Sam said as his brow furrowed.

Dean turned around and tried opening the door they had just come through, but it only revealed a couple making out in a janitor's closet. He closed it again, looking freaked out.

A brunette approached them and strode straight up to Sam. "Doctor," she greeted, then without warning slapped Sam's face harshly.

" _Ow!_ " he exclaimed, rubbing his cheek.

"Seriously," the brunette doctor continued.

"What?!" Sam asked.

The woman sighed and shook her head dramatically, before going on, "Seriously? You're brilliant, you know that? And a coward. You're a brilliant coward."

"Um," he rose an eyebrow at the presumably insane woman, "What are you talking about?"

This earned him another slap. "As if you don't know!" she accused, stalking off in the other direction.

Dean just gawked at her as if he was seeing a dream come true. "I don't believe this."

"What?" Sam asked, still rubbing his face and scowling.

"That's Dr. Piccolo," he gasped. "The sexy et earnest doctor at-"

He spun around and read the sign above the reception desk, "Seattle Mercy Hospital."

"You're kidding," Jay moaned, wiping her palm down her face. "We're not actually-"

"We're in  _Dr. Sexy, MD!_ "

 

The three of them went on through TV land until they had been through several programmes including a Japanese game show called 'Nutcracker'; a herpes commercial; a sitcom called 'Supernatural'; some cop drama (Jay's personal least favourite because it involved wearing sunglasses at night and making 'witty' comments that made her want to tear her own skin off).

At some point, Castiel had found them and tried to help them but he was quickly expelled by the Trickster- much to Dean's adamant concern.

At the moment, they were on the CSI program and Jay was watching the brothers make 'funny' remarks on the dead body, all the while wathcing the officer- he was sucking on a red lollipop.

"Good one, guys," the officer had laughed when Dean came round behind him, stake poised. In one swift motion, the point of it pierced the officer's heart and he fell to the floor.

None of the extras seemed to notice or care except another officer who started to laughed and morphed into the Trickster. "You've got the wrong guy, idiots!" he managed between laughs.

"Did we?" Jay raised an eyebrow.

The Trickster barely had time to acknowledge her remark before Sam was driving another stake into Loki's back.

As he fell onto the ground, there was a burst of static and the three hunters appeared in the original warehouse, wearing their original clothes  and looking down at the lifeless body of the Trickster.

She knew she should be happy.

She knew that she should be glad it was over...

...but Jay still felt an unexplainable pang of  _hurt_ that made her heart hurt.

 

It wasn't until she and Dean were back at the motel that they realised that their brother wasn't there with them.

Climbing into the impala, Dean hung up the phone when Sam hadn't replied and turned to Jay with a concerned look.

"Dean?" Sam's voice came from seemingly nowhere. "Jay?"

"Sammy?" Jay frowned, both of them searching around for their brother.

"Where are you?" Dean asked into the empty expanse of the car.

"I don't know," was the response.

Jay's eyes locked on a red light that flashed in time to Sam's words where the tape deck usually was; Dean followed her sightline and saw it too.

"Oh crap," cursed Sam. "I don't think we killed the Trickster."

As they drove, they discussed the current situation.

"Okay, stake didn't work. So, what, this is another trick?" Dean suggested, shrugging as he held onto the wheel.

"I don't know," Jay input. "Maybe the stake didn't work because it's not a trickster?"

"What do you mean?" Sam asked, his voice buzzing through the machine.

"You heard Cas. He said this thing was too powerful to be a trickster," she explained.

Dean nodded vigorously. "Yeah and did you notice the way he looked at Cas? Almost like he knew him."

"And how pissed he got when you brought up Michael and Lucifer," Sam added, agreeing.

"Son of a bitch," Jay whispered, her voice suddenly quiet.

"What?" the brothers asked at the same time.

Jay turned to grin at them both, triumphant, "I think I know what we're dealing with."

 

After pulling up at a clearing, Dean had rooted around in Sam/the impala's trunk before he had shouted into the sky to the Trickster. He appeared momentarily and greeted the boys and their sister with gaiety- turning Sam back into himself-, though he was less joyful when Sam threw a flaming lighter down on the floor that lit a ring of holy fire around him.

He congratulated them coldly before informing htem that his real name was Gabriel.

"Gabriel? The archangel?" Jay gasped.

"Guilty."

It was revealed that the archangel had put himself in his own private witness protection after all the fighting had gotten to be too much.

He just wanted it to be over.

Gabriel explained why Sam and Dean were the vessels, how it all had to end with them. But Jay and her brothers flat out refused to accept that and Dean demanded that Castiel be brought back from wherever he had put him. After a loose threat that involved frying themselves an archangel, Gabriel snapped his fingers and Cas appeared- not looking happy.

Dean turned towards the door.

"You're just gonna- you're gonna leave me here forever?" Gabriel gulped from where he was still trapped in his ring of blazing holy fire.

"No. No we're not," Dean growled. "'cause we don't screw with people the way you do. And for the record? This isn't about some prize fight between your brothers or some destiny that can't be stopped. This is about you being too afraid to stand up to your family."

Gabriel glared at them as Dean pulled the fire alarm; he turned his face up towards the ceiling and watched as the water fell from the sprinklers.

"Don't say I never did anything for you," was Dean's last comment before he left, closely followed by Sam and Castiel.

Jay hesitated a moment, her face as emotionless and blank as it could be, and turned back to Gabriel. He was already looking at her. "Family isn't all apple pies and monopoly," she whispered, her voice hushed but dangerous and the archangel listened. "Don't you dare complain about your family. You're fucking blessed." And with that, she turned around and marched straight out of the door, leaving the archangel simmering in his own stew behind her.


	5. Chapter 5

**Summary for the Chapter:**

> Gulping, Jay chewed on her lip and looked down at her feet.
> 
> "J-Jay?" Dean's voice dragged her gaze back up.
> 
> "Heh," Jay laughed awkwardly. "I-err..."
> 
> "You're the Princess!" Gabriel suddenly gasped. "You're-"
> 
> Gabriel promptly fell silent at the snap of Jay's fingers; Sam and Dean gasped in unison and exclaimed, "What the Hell?!"

**Notes for the Chapter:**

> Hello, everyone! So, took a couple days off, but here's the next chapter. Thanks for all the brilliant feedback , its what keeps this account going :) Hope you enjoy this chapter, not so much mature stuff or owt but I'm covering some plot. Hope you guys are in for the long haul because this is barely half way finished! XD have fun.

** _2015_ **

After they finished their breakfast, the two surrogate siblings and the two angels headed to the pool to meet more guests. This time, Jay bought a black two-piece swimsuit from the desk before she left the boys, and went to get changed in the women's changing rooms.

In the safe confinement of the changing rooms, Jay slumped down on a wooden bench and began to undress. She'd got down to her purple lace underwear before she gave up and collapsed against the locker behind her. Groaning loudly, she folded her arms over her face and tried not to replay the memory of Gabriel jerking off in the shower again.

"Hey, there."

Jay jumped and swore loudly at the voice that came out of seemingly nowhere. Opening her eyes properly, she saw that it was a young woman of about her age who had long rich blonde hair that waved down her shoulders in an elegant stream. The woman's skin looked soft and unbelievably pure and perfect; her large aqua blue eyes shone like ripples on a lagoon and were ringed with lengthy lashes. Full, pink lips stretched into a cool smile that bared white teeth. 

She was easily 5'6 and had long legs that had been cleanly shaven and protruded from under a short white satin dress that pinched delicately at her remarkable figure. A single gold band wrapped around her waist and matched the colour of her slim gold heeled shoes. She wore several gold necklaces and multiple sets of earrings. One particular necklace caught her eye: two bands of woven gold wire draped across her sternum and attached to the lower band were nine tear-drop shaped stones of amber. The largest of them was in the middle of the the others and a silver metal work shaped a bit like a pentagram but in swirling lines was embedded into it.

Extended towards Jay was a manicured hand that had deft fingers which were covered in rings and bracelets though the nails were left unpainted.

The Princess looked from the hand to the face and back, unsure of what it meant.

Smiling again, the woman retracted her hand and said, "You look a little troubled?"

"Oh," Jay managed, still slightly entranced by the incredibly beautiful woman in front of her. "I, err, it's nothing," she stammered, her mind fogging up from the close proximity of the attractive stranger.

"Man trouble?" she asked with a raised eyebrow.

Snorting, Jay nodded her head slightly. "Yeah, I suppose. Which is kinda ridiculous considering I'm at a couples' retreat."

The stranger smiled again and told her, "Beauty is the key, child."

Jay frowned and looked up at the woman. "Beauty?" she asked, incredulously, knowing full well that Gabriel could see her true face- which wasn't like other demons but not exactly Miss America either.

"Yes," she replied. "Beauty is the root of all love." And with that she stroked her fingers seductively down Jay's face before spinning on her heel and sidling out of the changing rooms.

The princess was left speechless and flustered.

 

* * *

** _2010_ **

Gabriel became a member of Team Free Will's family a few months after their last meeting in TV land. 

Sam, Dean and Jay were sitting fixed with fear on three plush red chairs. They'd been tricked into a hotel full of...well, Gods. Odin and Ganesh were in the middle of an argument- and Jay was in the middle of gathering her powers together for an attack on their captors- when Gabriel burst in through the double doors.

"Can't we all just get along!" he sang as he came through, turning the heads of all the Gods, Goddesses and hunters in the Grand Ballroom.

"Gabri-" Dean choked out before he couldn't say anything else.

Jay frowned and looked from Gabriel to Dean until she clocked on that Gabriel was using his powers to shut Dean up because...oh. The Gods didn't know.

They didn't now he was Gabriel.

The Princess fixed the archangel with a cold stare. His intrusion was an annoying blockade but with the sudden interruption, the Gods were caught off guard when Jay narrowed her eyes and a wave of power surged through the room. All of them were knocked flat on the ground and Sam and Dean looked toward Gabriel in a mixture of gratitude and shock.

Gabriel's eyes widened and his eyebrows furrowed. "That...wasn't me?"

"Then, who-?" Sam looked around the room.

Gulping, Jay chewed on her lip and looked down at her feet.

"J-Jay?" Dean's voice dragged her gaze back up.

"Heh," Jay laughed awkwardly. "I-err..."

"You're the Princess!" Gabriel suddenly gasped. "You're-"

Gabriel promptly fell silent at the snap of Jay's fingers; Sam and Dean gasped in unison and exclaimed, "What the Hell?!"

And that was how they found out that Jay was the Princess of Hell and also a demon/human/witch hybrid.

Lucifer never showed- he knew full well of Jay's powers- and Gabriel became a part of their family after that.

 

* * *

** _2015_ **

Following Jay's strange meeting with the beautiful woman, she got changed into her swimming costume in a sort of daze. It wasn't until Gabriel splashed her with water upon her entrace, that she registered anything else.

She squealed at the cold temperature and, via pure reflex, she flicked her wrist to shoot colder and icier water straight at Gabe's face.

"Gah!" he spluttered, grabbing Jay's foot and dragging her into the pool. 

Now that the cool water had sobered her up a bit, she checked around to see if there was anyone else in there but they were alone apart from Dean and Cas talking on a pair of lounge chairs ad a janitor mopping the floor.

"Sam at a gym class?" she asked Gabriel.

"Yoga, actually," Gabriel told her with a grin.

" _Yoga_?" Jay raised both eyebrows.

"Yup, it appears Gigantor is flexier than we thought," he smirked making Jay laugh. "I think he'll be joining us in a bit, though."

"Ok, cool," she mumbled, before ducking her head under the water to wet the rest of her hair and then smooth it flat against her head as she came back up. "Is there anyone here to even talk to?"

"Ol' McFreely over there?" Gabriel told her, gesturing towards the janitor.

With a quirk of the eyebrows, Jay blew a short raspberry- which inadvertently spewed a fountain of water straight into Gabe's face.

He spluttered and flicked his wrist at her, showering her in more water that was too much to have been from the actual pool. The princess recovered quickly from the attack and returned it with a 10ft wave that hovered in its form for a moment before crashing down on Gabe. The archangel was practically growling by the time the waves had stopped slamming against the side of the pool and had returned to their normal state of uncurrented calm.

Shaking himself off, Gabriel shot her a cold look, soon followed by a smirk as  he leapt on her and pushed her under the water. They could both breathe under water- since, technically, neither of them had to breath- and continued their squabble underwater.

Jay wrestled with the angel in fits of mutual laughter until she finally came up again, Gabriel joining her on the surface.

Looking around, Jay saw that the janitor had gone and now it was just them, Dean and Cas.

She was laughing when the mysterious woman's voice rang in her ears again. Her comment made Jay seethe and she inwardly battled against the grimace twisting her smile.

Gabriel must have seen it because he suddenly had a face of concern and he was looking at her as if he wanted to say something. "Jay?" he frowned. "What's wrong?"

She shook her head.

She wasn't about to indulge Gabriel in the pain she had felt  for some time.

For some years. 


	6. Chapter 6

**Summary for the Chapter:**

> "She's a demon, Bobby," Dean shot back. "And Crowley's daughter. What's to say she won't bring the whole of Hell down on us?"
> 
> "She's like a sister to you boys, isn't she?" Bobby retorted. "Well, I'm willing to bet that we're like family to her. And I know that girl and she puts family first. Always. You two idjits oughta understand that better than anyone."

**Notes for the Chapter:**

> Hello, my lovelies! Sorry it took a bit, but here you are! :) Enjoy there's some angst and the beginnings of some major angst but some counter-fluff so its all good ;)

** _2010_ **

To his credit, Cas took the revelation of Jay's secret pretty well.

"She is an abomination! The Princess is part demon and part witch, there is barely any of that creature that is human."

Even Bobby took it fairly calm.

"Try the iron! Try the salt! Can she get into the panic room? What kind of powers does she have? There's nothing about her anywhere! Balls!"

Jay was actually impressed by Gabriel's steady reaction.

"She's the Princess?! The Princess?! The fucking Princess of Hell?! We are screwed worse than Lindsay fucking Lohan!"

But real rationality came from Sam and Dean.

"She lied to us!"

"How could you?"

"Try the demon knife!"

"Will that work, Bobby?"

"The Hell is he supposed to know?"

"Well I don't fucking know, do I?!"

"Try the shotgun!"

"Shoot her!"

"You shoot her!"

"Why should I have to?!"

"You knew her longer!"

"She fucking helped me save you!"

"I knew she was there with you in Mystery Spot!"

"Yeah, she used her freakin' powers!"

"She has powers?!"

"She's a demon!"

"She's a witch, Sammy!"

"No, she's a demon/witch hybrid!"

"She's Crowley's freakin' daughter!"

"She's the Princess of fucking Hell!"

Jay sat there and took it all in as the five men shouted at each other, irrationally. After the clock had chimed one o'clock in the morning and she was still sat there on Bobby's old weathered couch listening to their arguments, she huffed and slumped back on the sofa, her head lolling backwards.

"You tired, Princess?" Bobby asked when he heard her sigh loudly, raising an eyebrow when she pried open her eyes.

"God, yes," she managed around a yawn.

Despite himself, Bobby smiled fondly, as if at his own daughter. Dean and Sam's hard faces visibly softened as well; something in Gabriel's eyes gleamed and she couldn't quite suppress the hitch in her heartbeat at that.

With a sigh, the matter was held in Bobby's eyes at seeing just how human and how Jay she still was. "Alright, come on, Kiddo. I reckon it's time for bed for all of us."

And with Bobby's words, the whole thing was dropped.

Only once more did Jay hear anything about the topic, between Sam, Dean and Bobby.

"Bobby," Sam said, pained. "What do we do, exactly? What can we do?"

"We don't do anything, boy," Bobby replied. "Jay has a past and a messed up family. Who here doesn't?"

"She's a demon, Bobby," Dean shot back. "And Crowley's daughter. What's to say she won't bring the whole of Hell down on us?"

"She's like a sister to you boys, isn't she?" Bobby retorted. "Well, I'm willing to bet that we're like family to her. And I know that girl and she puts family first. Always. You two idjits oughta understand that better than anyone."

Since then, Jay has been a real member of the Singer/Winchester/Angel family and not once has she regretted any of it.

* * *

 

** _2015_ **

A man and a woman walking in through the arch was enough to silence them.

"Oh, hello there," the woman greeted them. She had an auburn coloured bob that slanted off by her chin; her eyes were a velvety brown and her skin was aged but still pulled into a friendly smile when she saw other people already occupying the pool.

"Hey," Jay grinned back, swimming lazily to the edge of the pool and hauling herself out- missing the lustful way Gabriel's tongue shot out to wet his tongue as he tried not to eye Jay's round ass, even the perfect little trio of moles at the higher bit of her right cheek.

"The name's Julia," the woman told Jay, shaking the outstretched hand offered. "And this here is Pete."

"Jay," the Princess told her. Then gestured to each of her companions in turn. "And this is Cas, Dean and Gabriel."

"It's lovely to meet you," Julia beamed. "Isn't it, Pete?"

Pete sniffed and looked up from where he had been closely examining his socked feet in his sandals. "What's that?"

"Urgh," Julia scorned. "Listen, Pete! Please."

Jay cleared her throat and took herself out of the personal exchange.

"Oh, I am sorry," Julia apologised when she noticed Jay's awkwardness. "We came here to relax things and we're still fighting!" she sighed, laughing it off. "So, anyway," she cooed. "Who's here with who?"

Jay laughed lightly and turned to see Gabriel pulling himself out of the water and coming over to join her, putting an arm around her waist. "Well, I'm with Raspberries, here, and Cas and Dean are here with each other."

Chuckling at the nickname, Jay turned her head to look up at Gabe over her shoulder at the same time as he tilted his head down and for almost a full minute they searched each other's eyes.

"Say what you will, babe, you love my hair," Jay grinned at him.

He laughed and turned away from her, moving to sit on the sun bed next to Cas and Dean. Jay followed and gestured towards Julia and Pete, "Join us?"

"Certainly!" Julia accepted, sitting on the extra sun beds that Dean dragged around.

Jay moved to sit between Gabriel's legs and felt his arms come automatically to enclose around her hips in an endearing way that made Jay smile just a little more genuinely.

They quickly engaged in a deep conversation that soon revealed some clues to the investigation. Julia mentioned having seen a mysterious woman hanging around the rooms of the missing couples, and they both agreed to seeing cats around too.

Julia's account of the woman was what caught Jay's ear though "What did the woman look like?" she pressed.

"Well..." Julia chewed her lip. "She...was beautiful. Actually gorgeous. I mean she had long, blonde hair, she was wearing this white dress and she had these...these eyes."

Jay's eyes narrowed and her brow furrowed. "A lot of jewellery? One bigass amber necklace?"

"Yeah, actually she did," she nodded.

"That mean something to you?" Gabriel whispered in her ear, his breath warm and comforting.

With a subtle nod that only the archangel noticed, Jay continued, "What did she do exactly?"

"Umm." Julia chewed her lip. "Well, actually, she spoke to me. She asked me why I was here and...well I told her it was because Pete and I have been having some marital problems recently."

Jay nodded in a way that said go on...

"Well, its because...we both want children. But, umm, we can't..." she mumbled.

"I'm sorry," Jay said, sincerely.

Julia smiled at her sadly, "Thanks, hun." Then she looked back at her partner's face. "It was actually a while ago that I spoke with her, before we came back here. It was about a month ago but I saw her again when she was outside the missing couple's room."

"Wait, so you came here a month ago and talked to her the first time then you came back here this week and saw her outside the missing couple's room?" Dean clarified.

"Yeah," she answered. "Pretty much. Why are you so interested anyways?"

Gabriel shrugged. "Know your enemy."

Jay swatted him around the head from where she was still sitting in his lap. "Shut up, trickster," she grinned.

He blew a raspberry just below her ear and she squealed at him, Julia regarded them both with a smile. "Ah, I miss the honeymoon phase. You two really are a sweet couple," she cooed, wistfully.

* * *

 

** _2011_ **

Jay never really dated properly. Sure, she had frequent one night stands- something that had rubbed off on her from her time with Dean- but she never had a real long-term relationship.

Well, that wasn't entirely true.

The Princess did date. Once.

His name was Darol Drew and he was a 5ft 11 colossal douche bag.

But Jay hadn't known that when she first met him. It was maybe a month or so after her family had found out about her and she was looking around for good lays more often than usual for no other reason than the fact that she felt hollow inside now that her family knew how imperfect she was and she could no longer pretend that she was normal.

It was at a sleazy bar full of other sluttily dressed girls and guys all looking for only one thing. That was where she found Darol; he was leaning against the bar and eyeing her with a leer. He was tall (though not as tall as Dean or Sam, but who was?) with a muscular figure and fair hair that looked professionally styled. The first time she saw him, he was wearing loose jeans and a burgundy henley shirt.

After a number of shots- for confidence, she convinced herself- she sidled over to him, slightly wobbly.

His eyebrows bounced and he cocked a sly smirk. "What're you drinking, sugar?"

"Hmm," she murmured. "Alcohol." She was very drunk by this point.

Darol took full advantage and carried on. "So what's your name, sweetheart?"

"Jay," she told him, swaying noticeably. "Whazz yourzz?" she slurred.

"Darol," he smirked. "Darol Drew."

That night, Darol took Jay home. With Jay so heavily intoxicated, he did to her what she would have she would have pulled a gun on him for. Several times she said no and every time he carried on anyway, even rougher.

When she woke up the following morning, she was filled with a sick feeling of regret...as well as a covering of purple bruises. She hid it as best she could from Sam, Dean, Gabriel, Bobby and Cas but they did notice the hushed sobs that would come through her door.

* * *

 

** _2015_ **

Dean, Cas, Jay and Gabe met Sam in the bar that night, where he was already looking through witness accounts.

"Sup, Sammy," Jay grinned as she slid into the booth beside him.

He shot her an exasperated look but kissed her cheek in a casual gesture that both of her brothers did. "I'm still trying to figure this case out. I mean, there's something weird going on and I'm pretty damn sure that it is our thing but I have no idea what it could be."

"OK, well let me try something," Jay offered, swinging the laptop round to face her. She opened a new tab, consciously trying to ignore the fact that there was an open tab where Sam had been deleting his history, and searched up 'beauty woman couples'. She got the 'beauty' and 'woman' idea from the mysterious woman that had been hovering around the missing couples' rooms.But the results weren't all that enlightening.

"Add 'cats'," Dean suggested, leaning over her shoulder.

Again, nothing all that game-changing.

"Try 'love' instead of 'couples'," Gabriel tried. "I mean, if we're dealing with a creature or something then it's more likely that its gonna be more conventional?"

Jay followed the ideas and threw up her hands in frustration. "Great, now we got a load of crazy cat lady shit."

The archangel snorted.

"Oh," Jay exclaimed suddenly, an idea coming to mind. She quickly typed 'jewellery' but again there was nothing. "Dammit!"

"Hey," Gabriel smoothed a thumb over her shoulder. "We'll get talk to more guests, we'll get this case sorted. OK?"

Jay nodded and slumped her head on his chest. "'m tired," she mumbled into his shirt, and she was shattered.

Sam exchanged a look with Gabriel and Dean before Gabriel whispered to them. "I'll take her up to the room. Sasquatch you keep at the Enigma and Dean-o...try not to break that bed."

"What?" Sam asked, brows tugging together. "What?"

Gabriel just chuckled and pulled Jay up to standing with an arm around her waist. "C'mon Cupcake, let's get you to sleep."

"'m fine!" she complained, but her voice was thick with fatigue. "'m a freakin' demon/witch! Don't need sleep."

"Alright, demon/witch," Gabriel hummed in her ear, making her skin tingle elegantly. "You sing the full version of Cherry Pie on that table and I will admit that you do not need sleep."

Pushing herself off the archangel, she stood up straight and said, "OK, watch this, the."

But as she was stumbling over to the table directed, she felt Gabriel grab her arm and pull her back. "Jay, I was kidding," he told her. "I know you're a badass demon/witch who can just snap her fingers and equate it to a week's worth of sleep. But you still need your sleep, cupcake, and I'm not letting you headstrong your way out of this."

Reluctantly, she obliged and practically fell into the angel's open arms as they trundled into the corridor. She was almost fallling asleep when she realised that Gabriel was actually carrying her, slung over both his arms like a baby.

With a fond smile twisting his lips as he looked down at the sleeping princess, he pressed a soft kiss to her forehead.

Jay's heart sped and leapt in unadulterated joy. He didn't have to know she was awake.


	7. Chapter 7

**Summary for the Chapter:**

> "Come on, Princess," Gabriel murmured. "You're shattered and you need some sleep. Don't give me that look, I know just how little sleep you've been getting recently."
> 
> "Hmm, Gabe," Jay mumbled into his shoulder as he lay her on the bed. "Il mio angelo custode."
> 
> "I know, cupcake," he smiled. "I know."

**Notes for the Chapter:**

> So, BIGASS WARNINGS in this one- just to let you know. I'm not really spoiling anything by telling you that there is some non-consensual sex in this chapter (don't worry, it's all past memories and Gabriel fluff makes it all better). But dont let this put you off this chapter because it gets so much better :)  
> Also would just like to spread the word of Jared Padalecki's cause, Always Keep Fighting. I'm pretty sure you've all of it by now but just in case you haven't its a campaign to raise money and awareness for people suffering with depression, suicidal thoughts and other mental illnesses. This cause really hits home for me because I've been there before and one of my closest friends died quite recently because she cut herself and didn't pull trough in hospital.  
> I hope that you can at least spare a thought and some consideration for people whom are affected by this and if you want to read more then visit this website: https://represent.com/jared

** _2012_ **

Jay got very dependant on Darol very quickly.

Which was ridiculous of course because Jay was one of the most powerful creatures to walk the Earth. But Darol got her hooked on the drug that was himself. He made her too dependant on the relationship they had and it soon spiralled out of control.

"Get in the fucking bed!" Darol screamed from where he was sat on the bed in a stained white shirt.

Jay rolled over from where she was crouched on the couch trying to lose herself in the cyclone of her own thoughts.

"Oi! Whore!" He threw an empty beer bottle at the sofa and barely missed her head, but she still didn't flinch.

She felt too much pain inside her.

Finally having enough, Darol heaved himself off the bed and strode over to Jay's small figure. Without hesitation, he gripped a handful of Jay's vibrant pink hair which was actually fairly limp and unkempt- and pulled upward with a violent yank.

"Ah!" she squealed, trying to pull his hands away, gritting her teeth and digging her nails in to stop him. With a snap of her fingers she could make his head explode or call fifty Hell Hounds to tear him apart or bury him several hundred feet under the ground- but compared to him right then, she felt so powerless.

"When I tell you to do something," he bit out, tugging her frail body upward to meet his eye. "I expect you to fucking do it, you worthless bitch!"

Dragging her over to the filthy cheap motel bed, Darol flung her onto the sheets like a rag doll, crawling up and over her to straddle her hips possessively.

"Darol, please don't," she begged, hating how weak she sounded. "I can't, I just need to go home. My brothers will be expecting me by no- argh!"

The man above her tore off her shirt and ripped her flimsy tights out of the way, yanking down her panties in one swift movement. He took all of her in, in one smirk laboured leer that made Jay feel nauseated. "Hmm," he growled. "Just look at you. You're like the perfect little whore."

She grimaced; she loathed being objectified like that.

He didn't see and he definitely didn't wait; in one thrust, he slammed into her and clawed his nails down her thighs.

She wailed piercingly but it only spurred him on as he slammed into her again and again, each time causing a heart stopping pain that promised her that she wouldn't be able to walk or sit properly for the next few days. Darol merely carried on grunting away and thrusting hard into her even when the oh-too-familiar tears started stinging her eyes as she clenched them tight shut and gritted her teeth.

Stop. Please. Make it stop.

Please.

* * *

 

** _2015_ **

"Come on, Princess," Gabriel murmured. "You're shattered and you need some sleep. Don't give me that look, I know just how little sleep you've been getting recently."

"Hmm, Gabe," Jay mumbled into his shoulder as he lay her on the bed. "Il mio angelo custode."

"I know, cupcake," he smiled. "I know." Laying her down on the bed, he tucked her under the covers before perching beside her and stroking her hair down softly.

Snuggling down under the duvets, Jay purred at the touch and mumbled into the pillow, "Ti amo, lo sai?"

The rhythmic stroking of Gabriel's fingers stuttered a bit as he translated the comment in his head, but they then carried on and a small smile twinged his lips and echoed around in his eyes.

Once he was sure that the deep breathing and heavy rise and fall of her chest meant that she was asleep, Gabriel returned to his bed on the floor, dozing a bit to the fluttery snore that made his heart clench in fondness.

And maybe a tinsy winsy bit of love...

But who needed to know about that?

 

The next morning, Jay woke up surrounded by...cupcakes?

"What the-?" she exclaimed as she sat up and inspected the various mountains of assorted rainbow frosted cupcakes in all sorts of flavours with all sorts of toppings. "Gabriel!"

He appeared around the bathroom door with his hair still spiked slightly from how it had dried; he was wearing nothing but a pair of loose grey slacks. With a chortle that sounded too smug, the archangel told her, "Well, you've been so frustrated with this case, I thought some cupcakes and some baking might help."

She couldn't help the grin that burst through the scolding expression. Jumping up, she wrapped him in a tight embrace and smiled into his warm neck, "Il mio angelo custode. Ti amo."

Gabriel chuckled and wrapped his arms around her, his lips moving against her ear, "I know, cupcake, I know."

Breaking apart- most reluctantly on Jay's part- she grinned ear to ear at him when she spotted the oven, and all the kitchen equipment for baking in the corner that had definitely not been there last night. Without hesitation, she ran over to it and sorted the ingredients out as she readied the counter for cooking.

"I'll go tell the others to not wait," Gabriel told her, shrugging on a t-shirt and a jacket- the one that totally didn't make Jay heaten up under the collar. "Sam wants to head down to the sauna 'cause one of the staff reckons she saw something, and... I just wanna go steam up."

The princess barely acknowledged the comment but called over her shoulder, "OK, sweetie, see you later. Expect cupcakes when you come back!"

"Alright, Princess, don't make too much noise because it might raise a few eyebrows if anyone was to discover the bakery in our tropical room," Gabe warned with a fond smile.

Jay nodded and waved casually over her shoulder, already mixing ingredients in a massive bowl. With a flick of the wrist, she left the mixing bowl to carry on mixing itself and started on the icing while she snapped her fingers to turn up the heat on the oven.

Twirling her fingers in a lazy circle over her shoulder, the mountains of cupcakes diminished and sorted themselves out into a small pile around Gabe's bed on the floor.

While she was caught up in the rich smell of flour, sugar, butter and icing, Jay lost count of the number of cupcakes that flew steadily out of the oven (though it was certainly in the hundreds.) At some point she must've started singing too because the next moment she found her lips moving along to the radio she had conjured up from a though, which was playing Wheel in the Sky- Journey.

“Winter is here again oh Lord,  
Haven't been home in a year or more  
I hope she holds on a little longer  
Sent a letter on a long summer day  
Made of silver, not of clay  
I've been runnin' down this dusty road

Wheel in the sky keeps on turnin'  
I don't know where I'll be tomorrow  
Wheel in the sky keeps on turnin'

I've been trying to make it home  
Got to make it before too long  
I can't take this very much longer  
I'm stranded in the sleet and rain  
Don't think I'm ever gonna make it home again  
The mornin' sun is risin'  
It's kissing the day

Wheel in the sky keeps on turnin'  
I don't know where I'll be tomorrow  
Wheel in the sky keeps on turnin'

Woah-o-oh,” she sang, while she wondered to herself just why Gabriel had done this.

True, she had been rather stressed with this job- mainly because the whole situation was really hitting her hard (having to pretend to be a couple with Gabriel while she knew he didn’t return the feelings she had had towards him for a long time) and also because it wasn’t that long ago since she’d seen her ex-boyfriend on the news.

* * *

 

** _2015_ **

“Love you,” Darol whined, knocking Jay with his foot.

The man lay stretched out on the motel bed with a fresh beer in his hand, with Jay sitting perched on the farthest corner of the mattress.

“Jay,” he frowned. “Did you hear me?”

Almost unnoticeably, she nodded, but she daren’t reply.

“Well?” he growled. “Don’t you?” He prodded her with his foot again, slightly harder, making her rock precariously forward.

“Hmm,” she hummed, not trusting her voice.

She was the Princess of Hell.

She was a demon/human/witch hybrid, one of the most powerful beings on earth.

And she had never felt so powerless.

Without warning, Darol’s foot kicked her hard and she tumbled off the bed and into a heap on the floor with a shriek.

Once she’d regained her surroundings and had had time to calm down from the sudden fall, which had knocked her head hard on the corner of the table, she realised that Darol was laughing behind her.

“Oh, do that again!” he gasped between laughs, clapping his hands.

Jay bit her tongue hard enough to make it bleed, trying to stop herself from crying but the tears still stung her eyes. Just to shut him up, she forced a painful laugh but her hand still went to her right eye- where she could feel it starting to swell up a little where she had hit it. Oh crap, she thought, because she knew it was going to bruise and she was going to have a black eye.

And that was something she wouldn’t be able to hide from her family- Sam and Dean would go mental and search the country for someone to tear a new one; Cas and Gabe would tear the strip of universe apart to find who gave it to her; and Bobby would set every hunter and lead he had on the case of the person who hurt her.

“Oh, don’t be like that, babe,” he teased. “Have a fucking laugh, for once in your fucking life.”

And like that, she earned herself three fresh bruises on her stomach.


End file.
